The ruins of a large, historic stone building with multiple arches and a tall, narrow tower.

Chepstow Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Chepstow vacation rentals

Fridge, electric kettle, toaster, cookware/dishes/utensils

The Snug

The Snug
3.0 star property
Caerwent
The price is ￥53,478
￥64,174 total
includes taxes & fees
Jul 23 - Jul 24
The Snug
Fridge, microwave, oven, stovetop

The Elements Residence

The Elements Residence
Chepstow
The price is ￥174,765
￥198,795 total
includes taxes & fees
Jul 27 - Jul 28
The Elements Residence
Cottage | Interior

The Honey Pot

The Honey Pot
3.5 star property
Chepstow
The price is ￥86,159
￥103,391 total
includes taxes & fees
Jul 31 - Aug 1
The Honey Pot
Outdoor dining

Top Lodge

Top Lodge
2.0 star property
Caerwent
The price is ￥74,646
￥89,575 total
includes taxes & fees
Jul 24 - Jul 25
Top Lodge
Cottage | Living area | Fireplace

Bottom Lodge

Bottom Lodge
3.0 star property
Caerwent
The price is ￥74,646
￥89,575 total
includes taxes & fees
Jul 31 - Aug 1
Bottom Lodge
Cabin, Shared Bathroom (camping pod)

Broadstone Park Camping & Fishery

Broadstone Park Camping & Fishery
1.0 star property
Coleford
9.8 out of 10, Exceptional, (26 reviews)
"Amazing place for work or holiday. Clean affordable and great staff"
United Kingdom
Luke
The price is ￥10,268
￥12,322 total
includes taxes & fees
Aug 2 - Aug 3
Broadstone Park Camping & Fishery
Interior

A rural house on the edge of the Forest of Dean with 3 pubs within a short walk.

A rural house on the edge of the Forest of Dean with 3 pubs within a short walk.
Alvington
10.0 out of 10, Exceptional, (17 reviews)
"A truly wonderful stay in a wonderful little house! "
United Kingdom
Gaia C.
The price is ￥21,627
￥30,802 total
includes taxes & fees
Jul 21 - Jul 22
A rural house on the edge of the Forest of Dean with 3 pubs within a short walk.
Gym

The Metalworks

The Metalworks
2.0 star property
Windmill Hill
8.2 out of 10, Very Good, (11 reviews)
"Great accommodation Clean Great complementary beer Will be staying there again aoon"
United Kingdom
Pankaj
The price is ￥5,825
￥17,913 total
includes taxes & fees
Jul 26 - Jul 27
The Metalworks
Cottage | Property entrance

Beautiful 1-bed Cottage in Trellech

Beautiful 1-bed Cottage in Trellech
3.0 star property
Trellech United
9.2 out of 10, Wonderful, (25 reviews)
"Lovely staff and great space to relax."
United Kingdom
Eva
The price is ￥23,266
￥23,266 total
includes taxes & fees
Jul 22 - Jul 23
Beautiful 1-bed Cottage in Trellech
Property grounds

The Priory Cellars Abbots Leigh

The Priory Cellars Abbots Leigh
3.5 star property
Bristol
9.4 out of 10, Exceptional, (137 reviews)
"Excellent place to stay,I would highly recommend!"
United Kingdom
Ray
The price is ￥16,602
￥16,602 total
includes taxes & fees
Jul 20 - Jul 21
The Priory Cellars Abbots Leigh
Terrace/patio

The Orangery Apartment

The Orangery Apartment
4.0 star property
Bristol
9.6 out of 10, Exceptional, (77 reviews)
"Wonderful property and hosts. Great parking and facilities in property with plenty of space and stocked kitchen facilities. Would stay again"
United Kingdom
Janet
The price is ￥16,777
￥16,777 total
includes taxes & fees
Jul 23 - Jul 24
The Orangery Apartment
1 bedroom, iron/ironing board, WiFi, bed sheets

Anstey Heights - Apartment 4 - Hopewell

Anstey Heights - Apartment 4 - Hopewell
Easton
6.0 out of 10, (4 reviews)
"Terrible directions to the property. WiFi didn't work (router damaged) and TV cable couldn't connect due to damage, so no terrestrial viewing either. Absolute rip off for price paid. No response from property management. Floors stained and property in overall shabby condition."
United Kingdom
Adam
The price is ￥18,132
￥28,618 total
includes taxes & fees
Aug 2 - Aug 3
Anstey Heights - Apartment 4 - Hopewell
Premium Apartment, 2 Bedrooms | Living area | Smart TV

Quay Apartments Clarence House

Quay Apartments Clarence House
3.5 star property
St Julians
8.4 out of 10, Very Good, (155 reviews)
"All good. "
United Kingdom
Ifeoluwa
The price is ￥12,452
￥14,943 total
includes taxes & fees
Jul 20 - Jul 21
Quay Apartments Clarence House
TV

PREMIER SUITES Bristol Redcliffe

PREMIER SUITES Bristol Redcliffe
4.0 star property
Bristol Floating Harbour
8.6 out of 10, Excellent, (183 reviews)
"Excellent location, very easy to access all attractions . Spacious apartment "
United Kingdom
Gareth
The price is ￥16,203
￥19,443 total
includes taxes & fees
Jul 26 - Jul 27
PREMIER SUITES Bristol Redcliffe
Iron/ironing board, WiFi, bed sheets

Modern Studio in Desirable Clifton Area

Modern Studio in Desirable Clifton Area
Clifton
8.0 out of 10, Very Good, (7 reviews)
"Perfect location, quiet spot and beautiful neighbourhood."
United States
Joanne S.
The price is ￥16,821
￥25,559 total
includes taxes & fees
Aug 3 - Aug 4
Modern Studio in Desirable Clifton Area
1 bedroom, iron/ironing board, WiFi, bed sheets

Alma Studios - Apartment 3 - Hopewell

Alma Studios - Apartment 3 - Hopewell
Cotham
8.4 out of 10, Very Good, (9 reviews)
"Nice Big Space very well situated. But unfortunately quiet noisy because of the busy street."
United States
Marina
The price is ￥14,637
￥24,468 total
includes taxes & fees
Jul 20 - Jul 21
Alma Studios - Apartment 3 - Hopewell
Lounge

Orchard by UTDM

Orchard by UTDM
3.0 star property
Windmill Hill
The price is ￥13,901
￥42,896 total
includes taxes & fees
Aug 3 - Aug 4
Orchard by UTDM
Suite, 1 Bedroom | Hypo-allergenic bedding available, in-room safe, soundproofing

Redmayne House

Redmayne House
3.5 star property
Clifton
9.4 out of 10, Exceptional, (39 reviews)
"Lovely place to stay"
United Kingdom
Gail
The price is ￥21,800
￥26,160 total
includes taxes & fees
Jul 26 - Jul 27
Redmayne House
Studio | Exterior

Lovely 1-bed Loft in Newport

Lovely 1-bed Loft in Newport
3.0 star property
Caerleon
8.8 out of 10, Excellent, (5 reviews)
"Location very good for Caerleon. Clean and spacious "
United Kingdom
JAYNE
The price is ￥15,365
￥18,438 total
includes taxes & fees
Jul 20 - Jul 21
Lovely 1-bed Loft in Newport
Outdoor dining

Sunnyside Cottage - Rural 2-bedroom apartment

Sunnyside Cottage - Rural 2-bedroom apartment
Bristol
10.0 out of 10, Exceptional, (7 reviews)
"Lovely little place perfectly positioned for exploring Bristol.and the coast of the Avon."
United Kingdom
Kieran J.
The price is ￥25,166
￥28,880 total
includes taxes & fees
Jul 26 - Jul 27
Sunnyside Cottage - Rural 2-bedroom apartment
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chepstow Hotel Reviews

Future Inns Cardiff Bay

Future Inns Cardiff Bay

8/10 Good
"Other than the bed being slightly harder than used to it was a very good experience, staff were great and breakfast was good, thank you"
Shane 1-night trip
Posted 2 hours ago
Future Inns Cardiff Bay

Find out more about Chepstow

Search for holiday rentals in Chepstow on Expedia! You can easily find your home rentals, villas, holiday apartments in Chepstow using one of the methods below:

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Frequently asked questions

Can I find a vacation rental in Chepstow?

Yes, there are vacation rentals in Chepstow close to Chepstow Leisure Centre, or you can choose a secluded option if you'd like a relaxing place to stay. Visitors like the top-notch restaurants and spas in Chepstow. Allow lots of time to check out the riverfront and bars during your visit.

What are some of the best vacation home rentals in Chepstow?

Beautifully converted stone barn with amazing views towards the black mountains : This vacation home near Chepstow is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Chepstow?

Choose from 11 Expedia vacation rentals in Chepstow for a memorable vacation.

What’s there to see and do in Chepstow?

Wye Valley and River Wye are a couple of scenic spots to enjoy the outdoors, whereas Chepstow Museum is one of the cultural attractions. Chepstow Racecourse and St. Pierre Country Club are other places to visit while you're in town.

What’s a vacation rental in Chepstow like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Chepstow. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for families.